CA1250840A - Acides 4'-flavonecarboxyliques et leurs derives utilisables en pharmacie; preparation et applications - Google Patents

Acides 4'-flavonecarboxyliques et leurs derives utilisables en pharmacie; preparation et applications

Info

Publication number: CA1250840A
Authority: CA; Canada
Prior art keywords: formula; product; acid; ppm; carbon atoms
Prior art date: 1983-03-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000450354A

Other languages

English (en)

Inventor

Marie-Helene Creuzet

Gisele Prat

Francoise Guichard

Claude Feniou

Jacqueline Mosser

Henri Pontagnier

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asta Medica GmbH

Original Assignee

Cortial SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-03-24

Filing date

1984-03-23

Publication date

1989-03-07

1984-03-23 Application filed by Cortial SA filed Critical Cortial SA

1989-03-07 Application granted granted Critical

1989-03-07 Publication of CA1250840A publication Critical patent/CA1250840A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 26
GDILHIUGUNCNDU-UHFFFAOYSA-N 4-(4-oxochromen-2-yl)benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C1=CC(=O)C2=CC=CC=C2O1 GDILHIUGUNCNDU-UHFFFAOYSA-N 0.000 title description 3
239000002253 acid Substances 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
150000004702 methyl esters Chemical class 0.000 claims abstract description 17
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 16
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 15
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 14
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 7
125000000565 sulfonamide group Chemical group 0.000 claims abstract description 7
229910006074 SO2NH2 Inorganic materials 0.000 claims abstract description 6
150000001408 amides Chemical class 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
238000000034 method Methods 0.000 claims description 15
235000019441 ethanol Nutrition 0.000 claims description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 11
ZSSHNMZQDWSUJJ-UHFFFAOYSA-N n-(4-acetyl-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=O)C(O)=C1 ZSSHNMZQDWSUJJ-UHFFFAOYSA-N 0.000 claims description 7
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
235000005513 chalcones Nutrition 0.000 claims description 6
238000006798 ring closing metathesis reaction Methods 0.000 claims description 6
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 5
229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
125000005594 diketone group Chemical group 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
238000003381 deacetylation reaction Methods 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 10
FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
125000003158 alcohol group Chemical group 0.000 claims 1
239000002585 base Substances 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
150000002978 peroxides Chemical class 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 6
206010012601 diabetes mellitus Diseases 0.000 abstract description 4
230000002265 prevention Effects 0.000 abstract description 4
239000002934 diuretic Substances 0.000 abstract description 3
229940030606 diuretics Drugs 0.000 abstract description 3
238000002560 therapeutic procedure Methods 0.000 abstract description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
239000000047 product Substances 0.000 description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
125000003118 aryl group Chemical group 0.000 description 16
238000003756 stirring Methods 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
125000000896 monocarboxylic acid group Chemical group 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
-1 amino, hydroxyl Chemical group 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000005457 ice water Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000012071 phase Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
229960001701 chloroform Drugs 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
229960000443 hydrochloric acid Drugs 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
229940022682 acetone Drugs 0.000 description 4
FZDKBKLVQIYUKA-UHFFFAOYSA-N methyl 4-(7-chlorosulfonyl-4-oxo-3-propylchromen-2-yl)benzoate Chemical compound O1C2=CC(S(Cl)(=O)=O)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(=O)OC)C=C1 FZDKBKLVQIYUKA-UHFFFAOYSA-N 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 4
229960001052 streptozocin Drugs 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012156 elution solvent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
229940090044 injection Drugs 0.000 description 3
239000007924 injection Substances 0.000 description 3
MKEXWHUAMKQBGM-UHFFFAOYSA-N methyl 4-(7-amino-4-oxo-3-propylchromen-2-yl)benzoate Chemical compound O1C2=CC(N)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(=O)OC)C=C1 MKEXWHUAMKQBGM-UHFFFAOYSA-N 0.000 description 3
JXTZNZIHPPUKIF-UHFFFAOYSA-N methyl 4-(7-amino-4-oxochromen-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC(=O)C2=CC=C(N)C=C2O1 JXTZNZIHPPUKIF-UHFFFAOYSA-N 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
FBIITFGXWVSXBN-UHFFFAOYSA-N 4-(7-acetamido-4-oxo-3-propylchromen-2-yl)benzoic acid Chemical compound O1C2=CC(NC(C)=O)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(O)=O)C=C1 FBIITFGXWVSXBN-UHFFFAOYSA-N 0.000 description 2
PRYQTGOHQJXGEU-UHFFFAOYSA-N 4-[7-(methanesulfonamido)-4-oxo-3-propylchromen-2-yl]benzoic acid Chemical compound O1C2=CC(NS(C)(=O)=O)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(O)=O)C=C1 PRYQTGOHQJXGEU-UHFFFAOYSA-N 0.000 description 2
102000016912 Aldehyde Reductase Human genes 0.000 description 2
108010053754 Aldehyde reductase Proteins 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
208000002177 Cataract Diseases 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
210000000695 crystalline len Anatomy 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 2
229930182830 galactose Natural products 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 2
229960000367 inositol Drugs 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
VPPIOOQJYLZBPN-UHFFFAOYSA-N methyl 4-(7-acetamido-4-oxo-3-propylchromen-2-yl)benzoate Chemical compound O1C2=CC(NC(C)=O)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(=O)OC)C=C1 VPPIOOQJYLZBPN-UHFFFAOYSA-N 0.000 description 2
OQPFKELHYBYQFE-UHFFFAOYSA-N methyl 4-(7-acetamido-4-oxochromen-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC(=O)C2=CC=C(NC(C)=O)C=C2O1 OQPFKELHYBYQFE-UHFFFAOYSA-N 0.000 description 2
QEGHBVUMOBSIBK-UHFFFAOYSA-N methyl 4-(7-amino-3-hydroxy-4-oxochromen-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(O)C(=O)C2=CC=C(N)C=C2O1 QEGHBVUMOBSIBK-UHFFFAOYSA-N 0.000 description 2
201000001119 neuropathy Diseases 0.000 description 2
230000007823 neuropathy Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
208000033808 peripheral neuropathy Diseases 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
210000003497 sciatic nerve Anatomy 0.000 description 2
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
229960002920 sorbitol Drugs 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
WDZACGWEPQLKOM-UHFFFAOYSA-N 2-chloro-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(Cl)C(C)=C1 WDZACGWEPQLKOM-UHFFFAOYSA-N 0.000 description 1
ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
OPKOKAMJFNKNAS-UHFFFAOYSA-N 2-methylamino-ethanol Natural products CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
BVHATEDRYHHMGU-UHFFFAOYSA-N 4-(4-oxo-3-propyl-7-sulfamoylchromen-2-yl)benzoic acid Chemical compound O1C2=CC(S(N)(=O)=O)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(O)=O)C=C1 BVHATEDRYHHMGU-UHFFFAOYSA-N 0.000 description 1
JGKRUALBFKTTGS-UHFFFAOYSA-N 4-(7-acetamido-3-acetyloxy-4-oxochromen-2-yl)benzoic acid Chemical compound C=1C(NC(=O)C)=CC=C(C(C=2OC(C)=O)=O)C=1OC=2C1=CC=C(C(O)=O)C=C1 JGKRUALBFKTTGS-UHFFFAOYSA-N 0.000 description 1
XTGQAYMVTCUYNO-UHFFFAOYSA-N 4-(7-acetamido-3-ethyl-4-oxochromen-2-yl)benzoic acid Chemical compound O1C2=CC(NC(C)=O)=CC=C2C(=O)C(CC)=C1C1=CC=C(C(O)=O)C=C1 XTGQAYMVTCUYNO-UHFFFAOYSA-N 0.000 description 1
GACXZCPOJRSVOX-UHFFFAOYSA-N 4-(7-acetamido-4-oxochromen-2-yl)benzoic acid Chemical compound C=1C(NC(=O)C)=CC=C(C(C=2)=O)C=1OC=2C1=CC=C(C(O)=O)C=C1 GACXZCPOJRSVOX-UHFFFAOYSA-N 0.000 description 1
YTKVHQWYOWOREZ-UHFFFAOYSA-N 4-[7-[(2-morpholin-4-ylacetyl)amino]-4-oxo-3-propylchromen-2-yl]benzoic acid;hydrochloride Chemical compound Cl.C=1C=C2C(=O)C(CCC)=C(C=3C=CC(=CC=3)C(O)=O)OC2=CC=1NC(=O)CN1CCOCC1 YTKVHQWYOWOREZ-UHFFFAOYSA-N 0.000 description 1
JQQKQMJNPLNOBX-UHFFFAOYSA-N 4-[7-[2-hydroxyethyl(methyl)sulfamoyl]-4-oxo-3-propylchromen-2-yl]benzoic acid Chemical compound O1C2=CC(S(=O)(=O)N(C)CCO)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(O)=O)C=C1 JQQKQMJNPLNOBX-UHFFFAOYSA-N 0.000 description 1
REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 1
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
206010007749 Cataract diabetic Diseases 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
241000919811 Collyria Species 0.000 description 1
MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
208000032131 Diabetic Neuropathies Diseases 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000906446 Theraps Species 0.000 description 1
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001323 aldoses Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000002804 anti-anaphylactic effect Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
201000007025 diabetic cataract Diseases 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
KRMIBHIJJWJLJO-UHFFFAOYSA-N methyl 4-(4-oxo-3-propyl-7-sulfamoylchromen-2-yl)benzoate Chemical compound O1C2=CC(S(N)(=O)=O)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(=O)OC)C=C1 KRMIBHIJJWJLJO-UHFFFAOYSA-N 0.000 description 1
OWKWGXXDOKFQGQ-UHFFFAOYSA-N methyl 4-[7-(methanesulfonamido)-3-methylsulfonyloxy-4-oxochromen-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(OS(C)(=O)=O)C(=O)C2=CC=C(NS(C)(=O)=O)C=C2O1 OWKWGXXDOKFQGQ-UHFFFAOYSA-N 0.000 description 1
PLSGOULRDHCAJJ-UHFFFAOYSA-N methyl 4-[7-[(2-chloroacetyl)amino]-4-oxo-3-propylchromen-2-yl]benzoate Chemical compound O1C2=CC(NC(=O)CCl)=CC=C2C(=O)C(CCC)=C1C1=CC=C(C(=O)OC)C=C1 PLSGOULRDHCAJJ-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
NLGURIYTMITUSU-UHFFFAOYSA-N n-(3-hydroxy-4-pentanoylphenyl)acetamide Chemical compound CCCCC(=O)C1=CC=C(NC(C)=O)C=C1O NLGURIYTMITUSU-UHFFFAOYSA-N 0.000 description 1
OIEFZHJNURGFFI-UHFFFAOYSA-N n-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(NC(C)=O)=C1 OIEFZHJNURGFFI-UHFFFAOYSA-N 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
229940072033 potash Drugs 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000036325 urinary excretion Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Diabetes (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)

CA000450354A 1983-03-24 1984-03-23 Acides 4'-flavonecarboxyliques et leurs derives utilisables en pharmacie; preparation et applications Expired CA1250840A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8305013A FR2543140B1 (fr)	1983-03-24	1983-03-24	Nouveaux acides flavone-carboxyliques-4', leur methode de preparation et leur application en therapeutique
FR8305013		1983-03-24

Publications (1)

Publication Number	Publication Date
CA1250840A true CA1250840A (fr)	1989-03-07

Family

ID=9287281

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000450354A Expired CA1250840A (fr)	1983-03-24	1984-03-23	Acides 4'-flavonecarboxyliques et leurs derives utilisables en pharmacie; preparation et applications

Country Status (11)

Country	Link
US (1)	US4600788A (fr)
EP (1)	EP0125195B1 (fr)
JP (1)	JPS59181273A (fr)
CA (1)	CA1250840A (fr)
DE (1)	DE3466539D1 (fr)
ES (1)	ES8501385A1 (fr)
FR (1)	FR2543140B1 (fr)
MA (1)	MA20068A1 (fr)
OA (1)	OA07684A (fr)
PT (1)	PT78275B (fr)
ZA (1)	ZA842208B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62215581A (ja) *	1986-03-18	1987-09-22	Koichi Shiyudo	フラボンカルボン酸誘導体
JPH0753725B2 (ja) *	1987-10-08	1995-06-07	富山化学工業株式会社	４ｈ―１―ベンゾピラン―４―オン誘導体およびその塩、それらの製造法並びにそれらを含有する抗炎症剤
GB8804016D0 (en) *	1988-02-22	1988-03-23	Boots Co Plc	Therapeutic agents
GB9604709D0 (en) *	1996-03-05	1996-05-01	Imperial College	A compound
GB9603325D0 (en)	1996-02-16	1996-04-17	Imperial College	A compound
US6921776B1 (en)	1996-02-16	2005-07-26	Sterix Limited	Compound
US6506792B1 (en) *	1997-03-04	2003-01-14	Sterix Limited	Compounds that inhibit oestrone sulphatase and/or aromatase and methods for making and using
US20060241173A1 (en) *	1996-02-16	2006-10-26	Sterix Ltd.	Compound
AU2225597A (en) *	1996-03-05	1997-09-22	Imperial College Of Science, Technology And Medicine	Compounds with a sulfamate group
GB9807779D0 (en)	1998-04-09	1998-06-10	Ciba Geigy Ag	Organic compounds
FR2815033B1 (fr)	2000-10-06	2003-09-05	Negma Lab	Derives de 7-carboxy-flavones, porcede pour leur preparation et leur application en therapeutique
CN102391258B (zh) *	2011-09-13	2014-09-24	中山大学	氨基取代的黄酮类化合物及其制备方法和应用
TWI583677B (zh) *	2012-09-21	2017-05-21	日本臟器製藥股份有限公司	香豆素衍生物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH471113A (de) *	1965-01-29	1969-04-15	Merck Ag E	Verfahren zur Herstellung von wasserlöslichen Flavanoidderivaten
GB1461777A (en) *	1973-06-08	1977-01-19	Fisons Ltd	2-phenyl-4-oxo-4h-1-benzopyran derivatives
NZ193316A (en) *	1979-04-10	1984-07-31	Hoffmann La Roche	3-alkoxyflavone derivatives and pharmaceutical compositions

1983
- 1983-03-24 FR FR8305013A patent/FR2543140B1/fr not_active Expired
1984
- 1984-03-07 DE DE8484450006T patent/DE3466539D1/de not_active Expired
- 1984-03-07 EP EP84450006A patent/EP0125195B1/fr not_active Expired
- 1984-03-19 PT PT78275A patent/PT78275B/fr not_active IP Right Cessation
- 1984-03-22 ES ES530889A patent/ES8501385A1/es not_active Expired
- 1984-03-22 US US06/592,272 patent/US4600788A/en not_active Expired - Fee Related
- 1984-03-22 OA OA58258A patent/OA07684A/fr unknown
- 1984-03-23 JP JP59055962A patent/JPS59181273A/ja active Pending
- 1984-03-23 MA MA20290A patent/MA20068A1/fr unknown
- 1984-03-23 CA CA000450354A patent/CA1250840A/fr not_active Expired
- 1984-03-26 ZA ZA842208A patent/ZA842208B/xx unknown

Also Published As

Publication number	Publication date
DE3466539D1 (en)	1987-11-05
OA07684A (fr)	1985-05-23
MA20068A1 (fr)	1984-10-01
ES530889A0 (es)	1984-11-16
ZA842208B (en)	1984-10-31
PT78275B (fr)	1986-04-21
FR2543140A1 (fr)	1984-09-28
ES8501385A1 (es)	1984-11-16
EP0125195A1 (fr)	1984-11-14
US4600788A (en)	1986-07-15
JPS59181273A (ja)	1984-10-15
PT78275A (fr)	1984-04-01
FR2543140B1 (fr)	1985-06-21
EP0125195B1 (fr)	1987-09-30

Legal Events

Date	Code	Title	Description
2006-03-07	MKEX	Expiry

Publication	Publication Date	Title
US4591600A (en)	1986-05-27	3-hydroxyflavones: their preparation and therapeutic application
US3758506A (en)	1973-09-11	Phenoxyacetic acid derivatives
EP0222413B1 (fr)	1992-02-05	Dérivés de forskoline
EP0264586A1 (fr)	1988-04-27	Dérivés de l'hydantoine pour le traîtement de complications du diabète
JPS6160077B2 (fr)	1986-12-19
US4600788A (en)	1986-07-15	4'-flavonecarboxylic acids and pharmaceutically acceptable derivatives their preparation, and their application
JPS61200991A (ja)	1986-09-05	スピロ―３―ヘテロアゾリジン化合物、その製法及びそれを有効成分とする糖尿病合併症の予防及び治療剤
US2924603A (en)	1960-02-09	Aralkylbenzmorphan derivatives
EP0198456A2 (fr)	1986-10-22	Dérivés de la 1,7-naphtyridine et préparations médicales les contenant
EP0215736B1 (fr)	1990-08-29	Dérivés de xanthine, procédés pour leur préparation et leur utilisation comme médicaments
CA1075237A (fr)	1980-04-08	Derives de la purine
US3853921A (en)	1974-12-10	Process for the preparation of 3-cyanochromones
US3665074A (en)	1972-05-23	Certain benzofuran derivatives useful for relief of pain,inflammation,pyresis and tussive irritation
CA1068282A (fr)	1979-12-18	Derives de la 1,2-benzisoxazole et leur production
US3872108A (en)	1975-03-18	Novel chromone derivatives and the production thereof
US3637759A (en)	1972-01-25	Chromanes
JPH0131502B2 (fr)	1989-06-26
EP0030436A1 (fr)	1981-06-17	Dérivés de l'acide 2-hydroxyoxanilique et leurs sels, leur préparation et compositions pharmaceutiques les contenant
EP0566288B1 (fr)	1995-08-02	Dérivés de flavone
GB2107709A (en)	1983-05-05	Xanthines
US3882119A (en)	1975-05-06	Tetracyclic substituted phthalazine compounds
PL142254B1 (en)	1987-10-31	Process for preparing novel derivatives of ortho-condensed pyrrole
US4758561A (en)	1988-07-19	N-substituted 2-aminomethylene-1,3-indanediones for treating arterial hypertension and spasmodic conditions
EP0242230B1 (fr)	1990-10-03	Dérivés de pyrido[1,2-a]pyrimidine
US3547949A (en)	1970-12-15	Benzothiopyrone compounds